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Synthesis of Modified Fusicoccane Diterpenoids via Diverging MHAT Reactivity. 发散MHAT反应合成改性杂环二萜。
IF 2.3 4区 化学
Synthesis-Stuttgart Pub Date : 2026-03-01 Epub Date: 2025-11-27 DOI: 10.1055/a-2744-6756
Dylan W Snelson, Sebastian A Fernandez, Ryan A Shenvi
{"title":"Synthesis of Modified Fusicoccane Diterpenoids via Diverging MHAT Reactivity.","authors":"Dylan W Snelson, Sebastian A Fernandez, Ryan A Shenvi","doi":"10.1055/a-2744-6756","DOIUrl":"10.1055/a-2744-6756","url":null,"abstract":"<p><p>Cotylenin and fusicoccin diterpene glycosides modulate the stability of 14-3-3 protein-client interactions. Here, we report the divergent syntheses of representative aglycons, brassicicene (BR-I), and talarmalnoid B (Tal-B) by modification of Studer's Mukaiyama hydration variant.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"58 5","pages":"557-561"},"PeriodicalIF":2.3,"publicationDate":"2026-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13002104/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147500420","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Selective Reductions of Complex Pyridines via NTf-Pyridinium Salts. ntf -吡啶盐选择性还原络合吡啶。
IF 2.3 4区 化学
Synthesis-Stuttgart Pub Date : 2026-02-11 DOI: 10.1055/a-2784-2600
Celena M Josephitis, Andrew McNally
{"title":"Selective Reductions of Complex Pyridines via <i>N</i>Tf-Pyridinium Salts.","authors":"Celena M Josephitis, Andrew McNally","doi":"10.1055/a-2784-2600","DOIUrl":"10.1055/a-2784-2600","url":null,"abstract":"<p><p>Piperidines are widely found in biologically active compounds, and accessing these <i>N</i>-heterocycles from pyridines is a commonly used strategy. However, this approach is challenging when pyridines are embedded in complex structures, such as those found in pharmaceutical compounds. Here, we present a sequential approach to piperidines that commences with a hydride addition to <i>N</i>Tf-activated pyridinium salts. In this method, we combined tris(pentafluorophenyl)borane as a catalyst with a silane reducing agent to achieve 4-selective mono-reduction, and then combined it with metal-catalyzed reductions to obtain tetrahydropiperidine and piperidine derivatives. The process operates on a broad range of pyridines with various functional groups and substitution patterns, as well as on pyridine-containing drugs.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":" ","pages":""},"PeriodicalIF":2.3,"publicationDate":"2026-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC13061418/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147647298","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Chlorine-Bearing Asymmetric Center as a Stereocontrol Element in a Short Formal Synthesis of Steviol. 含氯不对称中心在甜菊糖短形式合成中的立体控制元件。
IF 2.3 4区 化学
Synthesis-Stuttgart Pub Date : 2025-09-04 DOI: 10.1055/a-2695-8576
Sharon E Michalak, Christopher D Vanderwal
{"title":"A Chlorine-Bearing Asymmetric Center as a Stereocontrol Element in a Short Formal Synthesis of Steviol.","authors":"Sharon E Michalak, Christopher D Vanderwal","doi":"10.1055/a-2695-8576","DOIUrl":"10.1055/a-2695-8576","url":null,"abstract":"<p><p>Steviol is one of myriad polycyclic terpenoids bearing oxygenation on the axially disposed C19 carbon. The presence of this C19 alcohol renders the C4 quaternary carbon stereogenic, issuing a challenge for stereoselective synthesis. Here we show that a suitably disposed chlorine atom at C2, coupled with the correct diastereomer of terminal epoxide that initiates cationic bicyclization, leads to the desired stereochemical outcome. Subsequently, the anisole terminating group undergoes Birch reduction that simultaneously reduces the C-Cl bond, removing the transient \"auxiliary\" and completing a short, highly stereoselective formal synthesis of steviol. This work provides another example of the power of removable C-X bonds for stereocontrolled synthesis.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":" ","pages":""},"PeriodicalIF":2.3,"publicationDate":"2025-09-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12456424/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145139288","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Unexpected Regiochemical Control in the Nugent-RajanBabu Reductive Epoxide Cyclization. Nugent-RajanBabu还原环氧化物环化过程中意想不到的区域化学控制。
IF 2.3 4区 化学
Synthesis-Stuttgart Pub Date : 2025-08-08 DOI: 10.1055/a-2680-2368
Nantamon Supantanapong, Scott W Niman, Christopher D Vanderwal
{"title":"Unexpected Regiochemical Control in the Nugent-RajanBabu Reductive Epoxide Cyclization.","authors":"Nantamon Supantanapong, Scott W Niman, Christopher D Vanderwal","doi":"10.1055/a-2680-2368","DOIUrl":"10.1055/a-2680-2368","url":null,"abstract":"<p><p>The Nugent-RajanBabu reductive epoxide cyclization has become a mainstay of alternative methods to accomplish classical, biomimetic, cationic polyene cyclizations. In most cases, the regiochemical control for the formation of decalins and perhydrophenanthrenes is exquisite, mirroring that obtained in cationic reactions, to the point where the 6-<i>endo</i> reactivity is anticipated even in the face of potential 5-<i>exo</i> processes. In our studies toward complex, polyoxygenated terpenoid natural products, we had cause to evaluate the reactions of α-alkoxy epoxides in these types of reactions, and we were surprised to uncover a means to control 6-<i>endo</i> vs 5-<i>exo</i> reactions based on the size of the protecting group on the α-oxygen. This knowledge opens up the possibility of rapid syntheses of highly oxygenated cyclopentane systems, in addition to the expected decalin scaffolds.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":" ","pages":""},"PeriodicalIF":2.3,"publicationDate":"2025-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12456417/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145139261","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of Benzo-Fused Cycloheptanones from Cyclobutanol Derivatives by a C-C Cleavage/Cross-Coupling/Enolate Arylation Sequence. 环丁醇衍生物C-C裂解/交叉偶联/烯酸酯芳基化合成苯并融合环庚酮。
IF 2.3 4区 化学
Synthesis-Stuttgart Pub Date : 2025-06-01 Epub Date: 2025-04-14 DOI: 10.1055/s-0043-1775469
Gwyneth L Pudner, Selena Dessain, Eric K Wu, Richmond Sarpong
{"title":"Synthesis of Benzo-Fused Cycloheptanones from Cyclobutanol Derivatives by a C-C Cleavage/Cross-Coupling/Enolate Arylation Sequence.","authors":"Gwyneth L Pudner, Selena Dessain, Eric K Wu, Richmond Sarpong","doi":"10.1055/s-0043-1775469","DOIUrl":"10.1055/s-0043-1775469","url":null,"abstract":"<p><p>Herein, we describe a convergent method for the synthesis of benzo-fused cycloheptanones from cyclobutanol derivatives and 1,2-dihaloarene electrophiles. The inherent ring strain of the cyclobutanol coupling partner is leveraged to drive a Pd-catalyzed C-C cleavage/cross-coupling. A subsequent intramolecular enolate arylation results in the formation of the benzo-fused seven-membered carbocycle in a one-pot sequence. A range of electronically diverse 1,2-dihaloarene electrophiles as well as various substituted cyclobutanols were investigated as cross-coupling partners.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"57 12","pages":"1982-1996"},"PeriodicalIF":2.3,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12705038/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145769698","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Concise Total Synthesis of Complanadine A Enabled by Pyrrole-to-Pyridine Molecular Editing. 利用吡咯-吡啶分子编辑实现了康帕那定A的简洁全合成。
IF 2.2 4区 化学
Synthesis-Stuttgart Pub Date : 2024-01-01 Epub Date: 2023-07-03 DOI: 10.1055/a-2107-5159
Brandon S Martin, Donghui Ma, Takeru Saito, Katelyn S Gallagher, Mingji Dai
{"title":"Concise Total Synthesis of Complanadine A Enabled by Pyrrole-to-Pyridine Molecular Editing.","authors":"Brandon S Martin, Donghui Ma, Takeru Saito, Katelyn S Gallagher, Mingji Dai","doi":"10.1055/a-2107-5159","DOIUrl":"10.1055/a-2107-5159","url":null,"abstract":"<p><p><i>Lycopodium</i> alkaloid complanadine A, isolated by Kobayashi et al. in 2000, is a complex and unsymmetrical dimer of lycodine. Biologically, it is a novel and promising lead compound for the development of new treatment for neurodegenerative disorders and persistent pain management. Herein, we reported a concise synthesis of complanadine A using a pyrrole-to-pyridine molecular editing strategy. The use of a nucleophilic pyrrole as the precursor of the desired pyridine enabled an efficient and one-pot construction of the tetracyclic core skeleton of complanadine A and lycodine. The pyrrole group was then converted to a 3-chloropyridine via the Ciamician-Dennstedt one carbon ring expansion. A subsequent C-H arylation between the 3-chloropyridine and a pyridine <i>N</i>-oxide formed the unsymmetrical dimer, which was then advanced to complanadine A. Overall, from a readily available known compound, total synthesis of complanadine A was achieved in 11 steps. The pyrrole-to-pyridine molecular editing strategy enabled us to significantly enhance the overall synthetic efficiency. Additionally, as demonstrated by a Suzuki-Miyaura cross coupling, the 3-chloropyridine product from the Ciamician-Dennstedt rearrangement is amenable for further derivatization, offering an opportunity for simplified analog synthesis.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"8 1","pages":"107-117"},"PeriodicalIF":2.2,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11636943/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89430381","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
SYNFORM ISSUE 2023/12 Synform issue 2023/12
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-14 DOI: 10.1055/s-0040-1720617
Matteo Zanda
{"title":"SYNFORM ISSUE 2023/12","authors":"Matteo Zanda","doi":"10.1055/s-0040-1720617","DOIUrl":"https://doi.org/10.1055/s-0040-1720617","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"25 9","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134992841","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Linked PDF of Table of Contents 链接的PDF目录
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-14 DOI: 10.1055/s-0040-1720098
{"title":"Linked PDF of Table of Contents","authors":"","doi":"10.1055/s-0040-1720098","DOIUrl":"https://doi.org/10.1055/s-0040-1720098","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"25 6","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134992844","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Regioselective Synthesis of 2,4- and 2,5-disubstituted 1,3-thiazoles from 2-oxo-2-(amino)ethanedithioates via Base Catalysed Cyclization 碱基催化环化2-氧-2-(氨基)乙二硫酸酯合成2,4-和2,5-二取代1,3-噻唑的区域选择性
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-14 DOI: 10.1055/a-2210-6357
Krishna Ravi Singh, C Santhosh, Kalleshappa Sheela, Marilinganadoddi P Sadashiva
{"title":"Regioselective Synthesis of 2,4- and 2,5-disubstituted 1,3-thiazoles from 2-oxo-2-(amino)ethanedithioates via Base Catalysed Cyclization","authors":"Krishna Ravi Singh, C Santhosh, Kalleshappa Sheela, Marilinganadoddi P Sadashiva","doi":"10.1055/a-2210-6357","DOIUrl":"https://doi.org/10.1055/a-2210-6357","url":null,"abstract":"We herein report efficient methods for synthesis of 2,4- and 2,5-disubstituted-1,3-thiazoles 3(a-i) and 5(a-k) by the cyclization of 2-oxo-2-(amino)ethanedithioates with TosMIC and α-haloketones in high yields. The structures 3a and 5a were confirmed based on X-ray crystallographic studies. In addition, investigation of ground state geometry, electronic and molecular structural properties, FMOs, global reactivity descriptors, MEP and NCI analyses predicted to access the information related to the stability, reactivity, and strength of the interactions present in the molecules by quantum chemical calculations. Further, the potency of derivatives tested against the SARS-Cov2 receptor (PDB ID: 7mc6) via molecular docking approach with binding scores of –6.0 to –8.4 kcal/mol.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"38 2","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134993136","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs 5-(三烷基)硅基戊-1-烯-4-炔-3-酮与肼的反应:合成含唑基发光物质的原始途径
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-13 DOI: 10.1055/s-0043-1763601
Alexander A. Golovanov, Ivan S. Odin, Kareem V. Gordon, Radik N. Itakhunov, Dmitry M. Gusev, Sergey A. Sokov, Anna V. Vologzhanina, Stanislav A. Grabovskiy, Ilya M. Sosnin, Anton I. Ukolov, Olga I. Orlova, Vladimir A. Lazarenko, Pavel V. Dorovatovskii, Darina D. Darmoroz, Anastasiia O. Piven, Tetiana Orlova
{"title":"Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs","authors":"Alexander A. Golovanov, Ivan S. Odin, Kareem V. Gordon, Radik N. Itakhunov, Dmitry M. Gusev, Sergey A. Sokov, Anna V. Vologzhanina, Stanislav A. Grabovskiy, Ilya M. Sosnin, Anton I. Ukolov, Olga I. Orlova, Vladimir A. Lazarenko, Pavel V. Dorovatovskii, Darina D. Darmoroz, Anastasiia O. Piven, Tetiana Orlova","doi":"10.1055/s-0043-1763601","DOIUrl":"https://doi.org/10.1055/s-0043-1763601","url":null,"abstract":"Abstract On the basis of the selective reactions of hydrazines with trialkylsilyl-substituted cross-conjugated enynones (pent-1-en-4-yn-3-ones) as fundamental building blocks, this work presents the developed common methodology for the synthesis of polysubstituted luminescent derivatives of acetylenic pyrazolines, pyrazoles, and combined polyheterocycles containing structural fragments from pyrazolines, isoxazoles, thiophenes, thiazoles, benzo[d]thiazoles, and benzo[d]imidazoles. In reactions with hydrazine and its monosubstituted aromatic and heteroaromatic derivatives, the mentioned pent-1-en-4-yn-3-ones, containing Me3Si, Et3Si, and t-BuMe2Si groups at the triple bond, give 3-(trialkylsilyl)ethynylpyrazolines. Following stages of desilylation and 1,3-dipolar cycloaddition with nitrile oxides, the 3-(trialkylsilyl)ethynylpyrazolines provide the formation of combined polyheterocyclic derivatives. Thus, a one-pot synthetic route to pyrazoline-containing isoxazoles from cross-conjugated enynones, arylhydrazines, and α-chlorobenzaldoximes has been developed. Some aspects of cyclocondensation mechanism and luminescent properties of synthesized azoles derivatives were examined.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"40 16","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136282055","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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